Process of distilling terpineol



Patented Sept. 1, 1936 I NliED sTA'rEs PATENT oFFlos I 2,052,743 PROCESSOF DVISTILLING TERPINEOL Carlisle H. Bibb, Pensacola, Fla., assignor toNewport Industries, Inc., Pensacola, Fla., a corporation of Delaware NoDrawing. Application December 4, 1935,

Serial No. 52,808

Claims. (01. 260-153) This invention relates to the production of a beapparent from the following detailed descrippure form of terpineolhaving an improved odor. tion and appended claims.

More specifically this invention relates to the The following exampleillustrates a preferred distillation of crude terpineol in the presenceof embodiment of the invention: 5 a caustic alkali to make possible abetter sepa- Exam le 5 ration of pure terpineol in high yield. p

C d rpin l i made mm y from A still is charged with 200 gallons of crudep p n i r an oil containing alpha terpineol oil containing about 85%tertiary alterpineol by agitating the oil with dilute acid such h l t inls, 14% of a hydrocarbon fracas dilute sulphuric acid until the pineneor alpha tion and about 1% of phenolic and acid constitu- 10 t rpin l ihy r to f p n hydrate ents. One gallon of 50% sodium hydroxidesolucrystalstion is added to the charge in the still. The still T e O ade t t p hydrate Crystals is then heated up to temperatures of about 86C. is removed by filtration or by steam distillation. t 6 pressure toremove the hydrocarbon l5 The t rpi hydrate crystals are h n suspendedfraction from the oil. After the hydrocarbon in dilute acid solution andsteam distilled to f ti h s b en removed, the still is heated form anoil which distills over with the steam. f th u t temperatures of about94 C. at This oil contains about 85% tertiary alcohols or 6 pressure, tdi till off the pure terpineol terpineols, of a hydrocarbon fraction,and fraction. A yield of about 80% pure terpineol is about 1% ofphenolic and acid compounds and t d represents the crude terpineol ofcommerce. Whil th b v temperatures may vary some- When the crudeterpineol is distilled at atmosh t depending upon the analysis of thecrude p pressure under Vacuum to remove the terpineol oil, thetemperatures listed indicate a lower boiling hydrocarbon fraction and tosubsepreferred per tion for an oil having the above qu n y ill v r thepi l i has been described analysis. obviously the temperatures 25 foundh the terpineol fraction h a w or indicated will also vary with avariation in the h r h d r f a phenolic na r F h mor ressures used inthe distilling apparatus. some decflmpositioh 0f the terpineols takesPlace Other caustic alkalies than sodium hydroxide due to the action ofacidic compounds and heat can be used with good results. For example,any

on the tertiary alcohols present which are classed lk li which willreact with a phenol can be used, 30 as terpineols. It is also impossibleto completely u h as sodium hydroxide, potassium hydroxide, free thedistilled terpineols from the hydrocaror lithium hydroxide and the like.b ns in h se hydr arb n re sl wly en- The chemical reactions involved inthe produce ated t ou ut t e distillation p tion of pure terpineolsaccording to this invention I have now discovered, how v t When a arecomplicated since it could not be anticipated 35 S ll am u t o Causticalkali is added to the that the caustic alkali would hold back thephestill during the distillation of the crude terpineol nolie compoundsand other acidic materials durther 15 I10 decomposition of theterpineols ing distillation because the alkali compounds of drocarbonsand also the terpineol fraction which such Substances h t d t d c mposeis separated has a highly mpr Odor Similar upon distillation due totheir weak acid character. 40

to a Very delicate mac helium? The amounts of caustic alkali used mayvary It is therefore an object of this invention to within a wide 1mm;since considerably less p p P terpineols P improved f amounts thanindicated in the above example are Anoth r o l f i invention is torecover operative and excessive amounts over the amount terpinetfls of ip purity from crude 1361- indicated are not inoperative. 45 DineolContainmg o I have also found that substantially the same A furtherobject of this invention is to distill results may be obtained bywashing the crude p terpineol from crude terpineol n ing oil terpineoloil with the alkali before distillation. in the presence of an alkaliwhich will react with However, this washing step can be avoided by aphenol. merely charging the alkali into the still. 50 A further objectof this invention is to separate From the above description, it shouldbe underpure terpineol in high yield from crude terpineol stood that Ihave prepared pure terpineol of imcontaining oil by distilling said oilin the presence proved odor and free from phenolic and acid comof acaustic alkali. pounds. I have also prevented the decomposi- Other andfurther objects of this invention will tion of the terpineols intohydrocarbons, such as 55 terpenes, during the refining operation and amtherefore able to obtain a higher yield of pure terpineols from crudeterpineol containing oil than was heretofore considered possible.

I am aware that many changes may be made and numerous details of theprocess may be varied through a Wide range without departing from theprinciples of this invention and I, therefore, do not purpose limitingthe patent granted hereon otherwise than necessitated by the prior art.

I claim as follows:

1. The process of producing pure terpineol which comprises distilling acrude terpineol containing oil in the presence of an alkali which willreact with a phenol and recovering the terpineol fraction.

2. The process of producing refined terpineol which comprises distillingcrude terpineol containing oils in the presence of a caustic alkali andrecovering the terpineol fraction.

3. The process of producing terpineol substantially free from phenolicbodies which comprises distilling crude terpineol in the presence ofsodium hydroxide and recovering the terpineol fraction.

4. The process of producing terpineol substantially free from terpenehydrocarbons which comprises distilling crude terpineol containing oilin the presence of small andrecovering the terpineol fraction.

5. The process of producing pure terpineols in high yield from a crudeterpineol oil containing about 85% tertiary alcohols, 14% of ahydrocarbon fraotion and about 1% of phenolic and acid constituentswhich comprises heating said oil in the presence of caustic alkali totemperatures of about 86 C. at 6mm. pressure to remove the hydrocarbonfraction therefrom, further heating the oil to temperatures of about 94C. at 6 mm. pressure to remove the pure terpineol fraction andrecovering said fraction.

' .i CARLISLEH. BIBB.

amounts of caustic alkali

